Trifluoroacetic acid → 1-Benzyl-3-(3,5-dichloro-2-fluoro-phenyl)-3-(trifluoromethyl)pyrrolidine

HRID 1500193Notes

Reaction equation

HRID 1500193 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([C:9]([C:11]([F:14])([F:13])[F:12])=[CH2:10])[C:3]=1[F:15].CO[CH2:18][N:19]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:20][Si](C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH2:25]([N:19]1[CH2:20][CH2:10][C:9]([C:4]2[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[C:3]=2[F:15])([C:11]([F:14])([F:13])[F:12])[CH2:18]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 871590141,5-Dichloro-2-fluoro-3-(3,3,3-trifluoroprop-1-en-2-yl)benzene

Product 1

HCID 871585151-Benzyl-3-(3,5-dichloro-2-fluoro-phenyl)-3-(trifluoromethyl)pyrrolidineYield 47.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1,5-Dichloro-2-fluoro-3-(3,3,3-trifluoroprop-1-en-2-yl)benzene (6.2 g) and N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine (4.7 g) were dissolved in dichloromethane (100 ml) and slowly added dropwise with a dichloromethane solution (8 ml) of anhydrous trifluoroacetic acid (0.15 ml) under ice cooling. Upon the completion of the dropwise addition, the reaction temperature was raised to room temperature and stirred overnight. The reaction solution was concentrated under reduced pressure, and the residue was purified by column chromatography to obtain 1-benzyl-3-(3,5-dichloro-2-fluorophenyl)-3-(trifluoromethyl)pyrrolidine (3.7 g).

Workup

  1. additionUpon the completion of the dropwise addition
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-2377215399684a16b24c1c595f2cadc3
Source dataset
uspto-grants-2015_12
Patent number
US09206122B2

Reaction notes

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